Jesters of Ravenloft: A D&D Podcast

40 Episodes
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By: Dumb-Dumbs & Dice

Jesters of Ravenloft is a D&D 5e podcast where a group of comedians are sucked into Dungeons & Dragons - and now it's up to them to become heroes and escape Ravenloft! A new episode drops every Friday and Saturday and, don't worry, there are NO SPOILERS for Strahd. Ranked in the top 50 fiction podcasts on Spotify and Apple Podcasts, check out Jesters of Ravenloft and find out why it's been downloaded more than 2M+ times now!

Jesters of Middle-earth - Episode 54 - The Friendly Dwarf
02/28/2026

The members of Wet Change were plagued with strange dreams about someone taking the hobbits to Isengard, the very fortress where Gandalf had been imprisoned. Guy recalled that he looked like Orlando Bloom in the dream and the rest of the troupe slowly recalled the actors that had appeared in their shared vision. They had never seen that version of The Lord of the Rings, but bizarrely, Tyler recalled having seen an entirely different version of the movie. In need of a good night’s sleep, Adam sniffed out a nearby settlement in Rohan. But can Del hide her Ga...


Jesters of Middle-earth - Episode 53 - They’re Taking the Hobbits to Isengard!
02/27/2026

The Fellowgroup got lucky as the orc commander struggled to land a blow, and eventually GanDelf redirected one of Adam’s missed strikes into the orc and the fight was won. Immediately, Tyler stormed into the water in search of Denethea and broke his toe on an orc helm, but Guy and Adam got him back to safety before he succumbed to the deep water and swift current. When they finally found Denethea, it was too late to save her and they were forced to admit she was truly lost to them. Del said some final words and they bu...


Jesters of Middle-earth - Episode 52 - Tyler’s Not Home Right Now
02/21/2026

The Fellowgroup found themselves facing a final, terrifying foe: the massive orc who had just felled Denethea. Tyler used his royal bearing to frighten the orc and held him off until his companions could join in the fight. Adam got there first and recklessly attacked, Guy used his uncanny skill with a bow to hit it from a distance, Yolo tried to contribute but got himself punted by the orc instead, and Del used her special wizard scissor skill to pin the orc’s arm and help her friends gain the upper hand. The Fellowgroup is finally working together ef...


Jesters of Middle-earth - Episode 51 - The King of Men and a Scared Orc
02/20/2026

As Denethea led some of the orcs away, the rest of the Fellowgroup tried to withstand attacks from the others. Guy rescued Yolo from the water and Frollum’s grasp, Adam struggled to don his armour again after it popped off, and GanDelf tried but failed to draw the orcs away from Denethea. Denethea made it to a boat and began leading the orcs downstream, but she was struck soundly with an arrow from a huge orc, and GanDelf and Tyler retaliated immediately. Gandelf drew upon her magic, and Tyler let the Aragorn within him take over as they bo...


Jesters of Middle-earth - Episode 50 - Everybody Gets an Arc
02/14/2026

The Fellowgroup faced off against orcs and Denethea! Tyler tried to talk Denethea down, but she refused to listen, and as she raised her sword, Yolo rushed her and together they tumbled towards the water below. Adam tried to fend off the orcs, but he got hit and his armour fell apart, Del couldn’t shield herself so she called out for help, and Tyler flopped onto an orc from above, crushing him and taking a life for the first time. Denethea came back to her senses and diverted the attention of the orcs away from the hobbits, as Gu...


Jesters of Middle-earth - Episode 49 - Words or Death
02/13/2026

The Fellowgroup was ambushed by orcs! Tyler ran to protect Yolo and the ring, but he heard Denethea threatening the hobbit, so he called for backup. Fighting their way to Tyler, Guy showed off his skill with the bow despite the melon stuck to his hand, Adam tossed melons at the orcs to trip them up, and Del unleashed an impressive flaming sphere on their foes. Meanwhile, Tyler tried to reason with Denethea, but she seemed to be too consumed by shadow until she heard Del cry out in pain in the distance and hesitated for a moment. Will...


Jesters of Middle-earth - Episode 48 - Orcs and Melons
02/07/2026

The Fellowgroup continued their journey southward towards Gondor. As their guide for this leg of their journey, Guy struggled to navigate the area, but they finally made it to the large hill of Amon Hen. Yolo spotted a stone seat at the peak and rushed up to it, while Denethea trudged after him in a sour mood and GanDelf remained ethereally aloof. Adam took over as the hunter after criticizing Tyler’s ability to only find watermelons, but then he could only find melons too, so he disguised them as eggs. As they argued about the source of the su...


Jesters of Middle-earth - Episode 47 - Fake People, Real Feelings
02/06/2026

The Fellowgroup remained for a while longer in the ruins of Lothlorien as Galadriel gave them crucial information about the Dark Lord. He now has two dragons and the Riders of Rohan in his service, and is no longer a disembodied eye. Luckily, his corporeal form is unstable, so there is still a chance of defeating him as long as he doesn’t possess the ring. Galadriel also warned Yolo that wearing the ring was like lighting up a beacon for the Nazgul, so they would have to move on quickly. She gave all the members of the Fellowgroup pa...


Jesters of Middle-earth - Episode 46 - A Tip from a Hot Elven Lady
01/31/2026

Despite the orc having shown herself to be Galadriel, Adam still saw an enemy and leapt up to attack. GanDelf stepped up to block him and was struck by a staggering blow, only to be spared by Denethea’s mithril deflector. They managed to sort out that they were all on the same side and Tyler healed everyone with his kingly presence. As conversation turned to the ring, Galadriel’s desire for its power grew, but GanDelf persuaded her that there was still hope, and the elf overcame the ring’s pull. Even with a powerful elf on their side...


Jesters of Middle-earth - Episode 45 - The Aspect of GanDelf
01/30/2026

The Fellowgroup hunkered down in the ruins of Lothlorien to hide from a fire-breathing dragon and a large group on horseback. Tyler confronted Yolo about putting on the ring again, but the hobbit became frightened when he realized he no longer had control over it, so GanDelf comforted him. Once the coast was clear, they emerged from hiding and came across an orc! They had planned to incapacitate it and question it, but Adam immediately got hit and the orc dispelled GanDelf’s magic. Luckily, their foe removed its orcish mask to reveal Galadriel herself. But can the Lady of...


Jesters of Middle-earth - Episode 44 - Was That a Dragon?
01/24/2026

The Fellowgroup arrived at the burnt, desolate landscape that used to be Lothlorien. While they battled their own dismay, they came across a charred and gored body bearing a sign that read “No safe harbours for the fellowship of the ring” and Guy recognized the figure to Celeborn, Lord of Lothlorien. They found only two elves still barely alive and learned that the destruction had happened at the hands of orcs, a fire-breathing dragon, and group called the Riders of Rohan. The headed towards the ruins of the elf sanctuary, but suddenly heard a flap of leathery wings and felt...


Jesters of Middle-earth - Episode 43 - The Desolation of Lothlorien
01/23/2026

The Fellowgroup was forced to stop and rest, as GanDelf found herself getting sleepy in her newly-acquired old age, and things began to escalate with Frodo. Tyler had convinced Yolo that they should let Frodo live, Adam didn’t believe the creature to be Frodo at all, they approached Frodo to get some answers, Frodo immediately said they should kill Yolo, and Yolo took his sword and lunged at Frodo. Once things calmed down, Frodo admitted to having murdered Grungus Took, but before they could decide what to do with him, the hobbit slipped away. As they approached Lothlorien, in...


Jesters of Middle-earth - Episode 42 - The Frodo We Know
01/17/2026

The Fellowgroup fled the Mines of Moria and escaped into the open air once more. GanDelf used her newfound magic to shatter the entrance and prevent any pursuit by their enemies, and they stopped at a mirror-clear lake to heal up. Del reflected on the strange duality of both her normal self and the wizard within her, Adam waded into the strange lake to wash up, Guy tried to find drinking water that wasn’t tainted by Adam’s filth, Frodo-Gollum had a full-on conversation with himself, but no one overhead it, and Tyler found watermelons. GanDelf began leading the...


Jesters of Middle-earth - Episode 41 - I Think My Brain’s Bad
01/16/2026

Gandalf the Grey was defeated and Del found herself suddenly full of magic, having finally taken up the mantle of a fallen character. The Fellowgroup distracted the Balrog with Guy’s arrows, Del’s magic missiles, and Adam’s fiery wad of paper. With the monster preoccupied, Adam rushed across the bridge, collecting his companions along the way, and crashed into the other side of the chasm. The Balrog seemed to be gathering itself again for another attack, but as it unfurled its wings, it landed upon Tyler’s tiny Tech Deck, tripped, and fell into the abyss. Can the Fell...


Jesters of Middle-earth - Episode 40 - The Thing that Used to be Del
01/10/2026

The Fellowgroup’s fight at the bridge of Khazad-DĂ»m became more desperate as the Balrog directed the goblins and undead dwarves towards Yolo. Tyler drew his sword to entice the Balrog away from Adam, but took a brutal hit from the monster’s flaming weapon, Del helped Tyler limp away as Guy carried the hobbits across the bridge, and Adam accidentally interrupted Gandalf’s powerful spell while trying to save him. As Gandalf made his last stand against the flaming monstrosity, his final effort was interrupted by an arrow to his throat, and as the wizard turned to ash, De...


Jesters of Middle-earth - Episode 39 - Put Those Corpses Down!
01/09/2026

The Fellowgroup faced off against Durin’s Bane, the Balrog of Moria, a massive creature bearing a flaming sword and whip. They all tried to distract it, Del shooting arrows and diving under its legs, Adam trying and failing to throw dwarves at it, Denethea clashing her sword, and Guy sprinting past it. Meanwhile, Tyler picked up the frozen Yolo, and the monster seemed to have eyes for only the ring-bearer. Gandalf and Denethea got hit hard, but the wizard managed to retaliate, and the two faced off with the terror before them. But can they hold back the fo...


Jesters of Middle-earth - Episode 38 - Turtles in Time in Moria
01/02/2026

The Fellowgroup found themselves trapped in a crypt facing undead dwarves, including Balin himself! Del struggled to hit anything, Guy used his new undousable torch to set corpses on fire, Adam dealt a strong blow in his rage, and Tyler started picking up the undead and hurling them away. Yolo attempted to escape by flinging himself down a hole in the floor, and the rest of them quickly followed, falling through a massive cavern and onto a huge pile of goblin corpses. As flames approached, they fled towards the Bridge of Khazad-Dûm and the exit from the mines. B...


Wrong Holiday Episode! Jesters of Ravenloft - 2.22 - Digging Holes
12/26/2025

The troupe is locked in combat with the Gargoyle King and five miniature gargoyles. New Rogue focused his powers entirely on keeping his goat safe, Shadow Nemesis tried to strike at the king, but hit Del instead, Tyler effectively conjured illusory clones of himself to draw the attention of the gargoyles, and Del psychically attacked with a Cronenberg-like jamboree band. The Doctor Deputy discovered that he couldn’t attack the gargoyle king unless it first attacked every member of the troupe, and with the stone giant swiftly smashing through Tyler’s illusions, will the troupe survive another blow?

Fe...


Wrong Holiday Episode! Jesters of Ravenloft - 2.21 - The Gargoyle King
12/26/2025

Wet Change entered the church in the Nameless Graveyard and, when Del realized it was Thanksgiving, they decided to celebrate and found some food and drinks. Rumpleforeskin made a berry jelly and baked a calzone inside themself, they all played cards, and the Doctor Deputy put on such an incredible show with the Tech Deck that Tyler gave it to him permanently. They all said what they were thankful for, received gifts from the Watchers, including a goat for New Rogue that he can pet without harming, and discovered that Shadow Nemesis had slept with a Sanguine. Now can...


Wrong Holiday Episode! Jesters of Ravenloft - 2.20 - Thanksgiving in Ravenloft
12/26/2025

We've taken the week off so our team can have a holiday before returning with fresh episodes! In the meantime, please enjoy a couple of episodes of Jesters of Ravenloft celebrating a completely different holiday!


In the previous episode...

The troupe left Protection Town and set off toward the Barren Hills. Del got her phone out and shared photos of them all in happier times and New Rogue connected again with Shadow Nemesis by reminiscing about Wet Change’s more bizarre sketches until they arrived at the Nameless Graveyard. Coming upon a ch...


Jesters of Middle-earth - Episode 37 - The King of Moria
12/20/2025

The Fellowgroup fought for their lives as the Watcher in the Water attacked them just outside the door into Moria. Del struggled to escape its grasp, but Guy slashed his way towards her, and Yolo and Denethea pulled them free. A gaunt creature claiming to be Frodo appeared and told Tyler the answer to the door’s riddle, and as the door opened, armoured dwarves hurled axes at the Watcher to cover their escape. Del was suspicious of the dwarves, but after Adam assured her that everything was fine, they let themselves be led inside to see the King of...


Jesters of Middle-earth - Episode 36 - Speak Friend, Idiot!
12/19/2025

The Fellowgroup negotiated with the elves and rangers and agreed that one of each could accompany them to the supposed party taking place in Moria. The troupe became annoyed with Yolo when he revealed his presence to their new travel companions, Guy spoke with Denethea, who mused allowed whether it might be nicer if someone more strong-willed could bear the Ring, and Del guided them all to a rock wall with a strange door next to a smooth lake. As they examined the door, they heard a cry. The ranger was gone and tentacles sprung from the water. Can...


Jesters of Middle-earth - Episode 35 - Horbit Melf Dwork
12/13/2025

The troupe broke camp, Del drank what was left of the navigation whiskey, and the Fellowgroup set off once more. They soon came across several rangers and elves having an argument over jurisdiction in the surrounding area, so Tyler and Del caught up and exchanged their thoughts about Denethea while Adam and Guy left to investigate. The rangers revealed they were also on the lookout for a hobbit carrying illicit jewellery and demanded to speak with the ranger in their Fellowgroup. The troupe regrouped and strategized their approach, but can they talk their way past these aggressive rangers and...


Jesters of Middle-earth - Episode 34 - A Dwarf and an Elf Walk into an Argument
12/12/2025

After a quick flashback to Frodo murdering Grungus Took, the Fellowgroup settled into their camp on the road the Moria. Del slept off her navigation whiskey, Denethea expressed a romantic interest in Del, and Tyler confronted Denethea. The Gondorian confessed she was frustrated that she’d be good ruler if not for her illegitimate birth, so Tyler made a deal that if she helped the Fellowgroup and proved to be a good person, he’d marry her and let her rule. Furthermore, Guy reported that she hadn’t done anything suspicious during her watch. Will the Fellowgroup’s burgeoning sense of...


Jesters of Middle-earth - Episode 33 - The Fellowgroup Goes South
12/06/2025

The Fellowgroup of the Ring left Rivendell and set off towards the Mines of Moria. They took stock of their burgeoning abilities and new weapons: Tyler’s ranger skills and reforged sword; Guy’s keen elf eyes and shiny mithril vest; Adam’s Wario-style everything; and Del’s uncanny ability to navigate while drunk. On the way, Tyler noticed Denethea staying uncomfortably close to him, so Del pretended to need the help of a strong woman and pulled the Gondorian’s focus, and Adam tried to hunt, but the thought of it brought back memories of how Tony Dumdum died. Is a...


Jesters of Middle-earth - Episode 32 - Yeet the Hobbit
12/05/2025

The Fellowgroup met to discuss their upcoming journey to Mordor. Gandalf brought out The Fellowship of the Ring on DVD, complete with a hand-written note from Peter Jackson to one of the film’s actors, and the troupe decided to explain away the synopsis as an alternate path that their journey could take. As they made their final preparations, Adam made an enemy of Glorfindel, Guy was disappointed to find Arwen only to learn she was looking for Tyler, and Arwen gave Tyler his sword, reforged, as a parting gift. They finally departed from Rivendell, but will everyone in th...


One Shots: Avernus - Episode 2
11/28/2025

We're unexpectedly off this week! In the meantime, we hope you enjoy another journey into hell in one of our One Shots: Avernus.


This arc features our awesome DM Tom McGee, Ryan LaPlante as Werner Ragnarok, Tyler Hewitt as Hambone, and Laura Hamstra as the elderly murder machine Maude Buggins! An entire city has disappeared and the members of The Stain were determined to avenge it! Our heroes were chasing down Thavius Kreeg and were forced to fight 3 death cultists. Hambone almost died and a winged demon told him he’d be in hell so...


Introducing... One-Shots: Avernus - Episode 1
11/28/2025

We're unexpectedly off this week! In the meantime, we hope you enjoy another journey into hell in one of our One Shots: Avernus. This 20-episode adventure features players Ryan LaPlante, Tyler Hewitt, and Laura Hamstra, alongside Dungeon Master Tom McGee. If you like these first 2 episodes, you can find the other 18 over at our One Shots podcast!


Enjoying One Shots?

- Consider supporting the show for as little as $1 a month to get BTS fun, an ad-free feed, and even add your own character to the podcast! (https://dumbdumbdice.com/join)

<...


Jesters of Middle-earth - Episode 31 - The DVD of Orthanc
11/22/2025

After an intensive day of councils, death, and crime scene investigation, the troupe settled down for the night. Adam inspected his new armour and was thrilled about its Wario-ness. Tyler was approached by Arwen, who told him they should not be held to a promise made when they were younger. They agreed to reevaluate their relationship after the business with the One Ring was concluded, and Arwen asked after Guy. Guy, meanwhile, fell asleep only to dream of dying at the hands of brutal orcs. Feeling unsettled, he went searching for food, and found Arwen in the kitchens. Could...


Jesters of Middle-earth - Episode 30 - The Complete Uninhibited Guy Experience
11/21/2025

The troupe gathered more evidence at the scene of the crime. Del deduced that the suspect must be short, Tyler noticed that Yolo’s feet were not in fact muddy, and Guy failed to stop Elrond from entering the brothel room. So, back in the privacy of their rooms, they shared their theories. Tyler told them that Grungus had split up Frodo and his boyfriend, Sam, so Grungus clearly had no shortage of enemies with grudges. Plus, they worried about Yolo’s fate if they were wrong, and were aware that he was needed as the ring-bearer, so they deci...


Jesters of Middle-earth - Episode 29 - CSI: Middle-earth
11/15/2025

Grungus Took’s death took the troupe by surprise. Guy and Del investigated the scene of the crime and hoped the trail of muddy footprints would lead them to a suspect. Adam went to report the news to the dwarves, but they wouldn’t let him in to see his father. Even worse, the one dwarf that Adam had actually connected with died suddenly in a freak accident. Tyler was left to console Yolo and talk him through his conflicting feelings, but when he brought Yolo in to see the body, Guy and his keen elven eyes noticed that Yolo...


Jesters of Middle-earth - Episode 28 - A Chorus of ‘WAAAAAH’s
11/14/2025

After Gandalf retold the tale of his imprisonment by Saruman, he told Del that the dwarves suspected that Grungus had sold them out and used the ring to get the dragon’s treasures for himself, so they headed to the brothel to question Grungus directly. Adam and Guy also went there looking for Grungus, but arrived shortly after the others to find the hobbit had been stabbed to death. Meanwhile, Tyler convinced Yolo to trust him, and Yolo revealed that Grungus had stabbed a small riddle-obsessed creature in cold blood to steal the ring. Is there any hope of de...


Jesters of Middle-earth - Episode 27 - The Last Horny House
11/08/2025

With the Fellowgroup’s mission decided, the troupe tied up loose ends in Rivendell. Tyler cleared the air with Denethea and was having a pleasant moment with Arwen when Guy burst in, smitten with the Liv Tyler lookalike. The boys wondered if Arwen was meant to end up with Guy instead. Meanwhile, Adam recalled his character dying in a dragon’s fiery breath and regained his father’s approval, so Gloin asked Adam to check in on their kin at the Mines of Moria, but first they would interrogate Grungus to find out what really happened at the Lonely Mounta...


Jesters of Middle-earth - Episode 26 - Am I a Ghost, Daddy?
11/07/2025

After a surprise meeting with Werner Herzog, the Fellowgroup attended the Council of Elrond, where they learned the history of the Rings of Power and debated what to do with the One Ring. Guy and Tyler both immediately put forth that it should be destroyed, and after some debate, Tyler pointed to Grungus Took as proof that the ring only corrupted people and made them horrible. Gloin then volunteered Adam to help destroy the ring, and Guy, Tyler, and Del all agreed to go on the quest too. The Fellowgroup then began to get healed, armed, and armoured, and...


Jesters of Middle-earth - Episode 25 - The Worst Halfling You’ve Ever Seen
11/01/2025

The Fellowgroup haven’t made any friends in Rivendell. Adam’s kin saw through his lies and beat him up until someone brought news that Grungus Took was nearby, Guy discovered that saying the name J.R.R. Tolkien injured his fellow elves, and at the Gondor camp, Denethea declared she wanted the ring for herself, then stabbed Del when Tyler said it wasn’t theirs to give to her. Del and Tyler were saved by the arrival of Gandalf, and once the wizard got the troupe alone, he revealed that he knew they didn’t belong in Middle-earth and prod...


Jesters of Middle-earth - Episode 24 - Violence at the Last Homely House
10/31/2025

The Fellowgroup arrived in Rivendell and met people who seemed to know them! Guy learned that he’s immortal, his father is the king of Mirkwood, and the other elves want Yolo’s ring for themselves. Del gave Tyler relationship advice about the Arwen situation before they met Denethea, daughter of the Steward of Gondor. Once Tyler assured her that he didn’t want to claim any throne, Denethea spoke about her brothers, Faramir and Boromir, and their fixation on the ring. Adam, meanwhile, cornered himself into improvising the tale of his supposed escape from the Lonely Mountain, but is he c...


Hack N Slash - Episode 4
10/25/2025

During our week off, please enjoy the continuation of our "Monster of the Week" miniseries: HACK N SLASH!


HACK N SLASH is a four-part improvised comedic mini-series featuring Ryan LaPlante as the Keeper, Del Borovic as Shadow Lady, and three new voices: Josh Halbot as Bloody Mark, Kevin Hanna as Tailspin, and Pam Sparrow as Dr. Belladonna. This “Monster of the Week” adventure features four monsters who find out they’re being replaced by upgraded versions of themselves and must fight to stay alive.​


Find more episodes on Spotify (https://o...


Hack N Slash - Episode 3
10/25/2025

During our week off, please enjoy the continuation of our "Monster of the Week" miniseries: HACK N SLASH!


HACK N SLASH is a four-part improvised comedic mini-series featuring Ryan LaPlante as the Keeper, Del Borovic as Shadow Lady, and three new voices: Josh Halbot as Bloody Mark, Kevin Hanna as Tailspin, and Pam Sparrow as Dr. Belladonna. This “Monster of the Week” adventure features four monsters who find out they’re being replaced by upgraded versions of themselves and must fight to stay alive.​


Find more episodes on Spotify (https://o...


Hack N Slash - Episode 2
10/24/2025

During our week off, please enjoy the continuation of our "Monster of the Week" miniseries: HACK N SLASH!


HACK N SLASH is a four-part improvised comedic mini-series featuring Ryan LaPlante as the Keeper, Del Borovic as Shadow Lady, and three new voices: Josh Halbot as Bloody Mark, Kevin Hanna as Tailspin, and Pam Sparrow as Dr. Belladonna. This “Monster of the Week” adventure features four monsters who find out they’re being replaced by upgraded versions of themselves and must fight to stay alive.​


Find more episodes on Spotify (https://o...


Introducing... Hack N Slash - Episode 1
10/24/2025

Due to some unforeseen circumstances, we'll be taking this week off. We'll be back next week, but in the meantime, please enjoy our "Monster of the Week" miniseries: HACK N SLASH!


HACK N SLASH is a four-part improvised comedic mini-series featuring Ryan LaPlante as the Keeper, Del Borovic as Shadow Lady, and three new voices: Josh Halbot as Bloody Mark, Kevin Hanna as Tailspin, and Pam Sparrow as Dr. Belladonna. This “Monster of the Week” adventure features four monsters who find out they’re being replaced by upgraded versions of themselves and must fight to sta...